Download PDF by Royal Society of Chemistry, W. Parker, Parker W: Alicyclic Chemistry: Volume 4: A Review of Chemical

By Royal Society of Chemistry, W. Parker, Parker W

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1974,4, 243. H. K. Hall, jun. and R. E. Yancy. J. Org. , 1974,39,2862. F. E. Ziepler and J. A. Kloek, Tetrahedron Letters, 1974, 315. ~~~ In the case of l,1-dimethylallene, the 3: 1 ratio of products (232a) and (232b) was found to be constant over the range 80-150°C, indicating that the two isomers are not formed by independent pathways, but via a common biradical(231) in different conformations. )-C= + CF,C-CCF, F3CA 6 , EF3+ (232a) CF3 c@(232b) Photochemical rearrangement of aj3- or flyunsaturated ketones may give rise to methylenecyclobutanols.

I. B. Avezov, 1. G. Bolesov, and R. Y. Levina, Zhur. org. , 1974, 10, 2114 (Chem. , 1975, 82, 42 990). Z. Yoshida, Yuki Gosei Kagaku Kyokai Shi, 1974,3& 89 (Chem. , 1974,81,49294). J. Ranfaing, B. Calas, J. M. Fabre, and L. Giral, Tetrahedron Letters, 1974, 1439; see also M. Larcheveque. A. Debal, and T. Cuvigny, Bull. chim France, 1974,1710. G. Stork and J. F. Cohen, J. Amer. Chem. , 1974,%, 5270. 43 Three- and Four-membered Rings formed in preference to cyclopentanes. This has been adapted into a general synthesis of functionalized cyclobutanes, and is illustrated by the preparation of ( f)-grandis01 (Scheme 16).

40 Alicyclic Chemistry Ph HSO; Ph + Ph CO,H 0 0 Scheme 14 The dehydrobromination of the dibromo-ketone (164)affords 2,2,5,5-tetramethylbicyclo[4,l,O]hept-l(6)-en-7-one (163,the most highly strained ring-fused cyclopropene yet ~ y n t h e s i z e d . ~ ' ~ Elimination reactions of cyclopropyl halides can provide a simple route to cyclopropenes, since the former are readily available by semi-reduction of the dihalogenocarbene adducts of olefins. This compound has now been prepared containing ' M.

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Alicyclic Chemistry: Volume 4: A Review of Chemical Literature (Spr Alicyclic Chemistry (Rsc)) by Royal Society of Chemistry, W. Parker, Parker W

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